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Florida Keys Festivals: A Quick Guide To Top Celebrations (2023)

florida keys festivals

Ready to find the best Florida Keys festivals? As someone who’s called Florida home for quite some time and made countless trips to the Florida Keys, I’ve got to tell you, there’s something truly special about this place.

Are you planning your trip to the Florida Keys last minute?


If you are booking your trip to the Florida Keys last minute, we have you covered. Below are some of the top tours, hotels, and more!

⭐Top Experiences and Tours in the Florida Keys:

  1. Snorkel Adventure and Sandbar (the top seller!)
  2. 1.5 Hour Waverunner Tour (Highly rated!)
  3. Sunset Cruise from Cheeca Resort (Gorgeous Photos!)
  4. Glassbottom Boat Tour (So popular!)
  5. Key West Sunset Sail & Full Bar (Live music too!)
  6. Key West Shark Adventure (For adrenaline junkies)

🛌  Top Hotels in the Florida Keys:

  1. The Capitana Key West (Key West)
  2. Tranquility Bay (Middle Keys)
  3. Bakers Cay Resort (Upper Keys)

🚗  Looking for the best way to get around the Florida Keys? Click here to check rental car rates for Florida!

The festivals down there? They’re not just events; they’re experiences that get right to the heart of what the Keys are all about. From the lively energy of Key West to the laid-back charm of the Lower Keys, I’ve seen it all, and I’m excited to share some of my favorite parts with you.

You might be into seafood, art, music, or just looking for a good time in the sun. Whatever it is, the Keys have got you covered.

Whether you’re planning on attending the wild Fantasy Fest, enjoying the tunes at the Key West Song Writers Festival, or indulging in the freshest seafood you can imagine. Each festival has its own unique flavor and vibe that’s worth exploring.

So, if you’re planning a trip down to the Keys, or just curious about what’s going on in this tropical paradise, stick with me.

In this guide, I’ll give you the inside scoop on the top celebrations and festivals, all from the perspective of a long-time traveler and Florida resident.

No fluff, just the good stuff. Let’s dive into the vibrant world of Florida Keys festivals and see what adventures await!

Overview of Florida Keys Festivals

The Florida Keys are home to a diverse range of festivals that cater to various interests. From celebrating women to exploring wildlife, here’s a glimpse of what you can expect.

Key West Festivals

Key West is a hub for some of the most exciting festivals in the Florida Keys. From Pride celebrations to songwriters’ showcases, here’s what awaits you.

Celebrations in Key West

  • Key West Pride: Celebrate love and diversity in early June on Duval Street, a key location for Key West LGBTQ events.
  • 27th Annual Key West Song Writers Festival: Held in May, showcasing over 200 songwriters across various venues.
  • Key West BrewFest: A September event for craft beer enthusiasts at Southernmost Beach Resort.

Art in Florida Keys Festivals

assorted hanging bath bombs

Key West arts are celebrated in the Florida Keys with a rich and vibrant scene. From traditional paintings to unique sculptures, these festivals offer a feast for the eyes.

Artistic Expressions

  • Old Island Days Art Festival: Showcases diverse works by talented Florida Keys artists, held at the Custom House Museum.
  • Key West Craft Show: Browse through authentic crafts and arts.
  • Art in the Garden: Held at Key West Tropical Forest & Botanical Garden, featuring nature-inspired art.
  • Art Festival Weekend in Key Largo: Celebrate local arts and culture in mid-April at the Island Market Place.

Ernest Hemingway and Festivals

man sitting on bench statue

The legendary author Ernest Hemingway is celebrated in the Florida Keys through a unique festival that pays homage to his life and work.

Hemingway Days

  • Hemingway Days: An annual festival featuring activities like the Running of the Bulls and Hemingway Look-Alike Contest, held at Sloppy Joe’s Bar.

Seafood and Festivals in Florida Keys

Seafood lovers are in for a treat with festivals dedicated to the fresh and delicious seafood of the Florida Keys, including the Lower Keys Marathon and Keys Marathon Islamorada.

Culinary Delights

  • Florida Keys Seafood Festival: Held annually in January, showcasing fresh seafood.
  • Original Marathon Seafood Festival: A family-friendly gathering in March.
  • Key West Lobsterfest: Celebrate the lobster season in August.

Fishing Tournaments in the Florida Keys

a boat on the water

Anglers can enjoy a multitude of fishing tournaments in the Florida Keys, ranging from high-stakes competitions to friendly challenges, including the famous Key West Fishing Tournament.

Angler’s Paradise

  • Key West Fishing Tournament: A multi-month competition from December to July, targeting over 40 species of fish.
  • Florida Keys Fishing Tournaments Schedule: A comprehensive list of challenges throughout the year.

Cultural Festivals

green and white floral textile

Experience the unique flavors, creativity, and diversity of the Keys through various cultural festivals.

Cultural Celebrations

  • Conch Republic Independence Celebration: Commemorates the founding of the Conch Republic.
  • Key Lime Festival: A tribute to the unique Key lime fruit.
  • Mango Fest: Celebrate the luscious mango fruit during the summer.
  • Tropical Heat: An all-male festival geared toward gay men.
  • Womenfest: A popular LGBTQ festival for women.

Physical Activities in Festivals

For fitness enthusiasts, the Florida Keys offer a range of exciting physical activities during various festivals.

Active Adventures

  • 5k Runs: Scenic routes for runners of all levels.
  • Diving Experiences: Explore the rich marine life and coral reefs, including a visit to the Diving Museum.
  • Trails: Enjoy leisurely walks or challenging hikes.

Street Fairs and Attractions

Explore the vibrant local culture and natural beauty of the islands through street fairs and attractions, including the famous Duval Street.

Street Celebrations

  • Key West Lobsterfest: A street fair from August 10-13, 2023, on Duval Street.
  • Art Under the Oaks: An annual festival in Tavernier in January.

Florida Keys Educational Events

silhouette of man riding on blue kayak on sea during sunset

Enhance your understanding of the region’s environment, history, and even space exploration through various educational events.

Learning Opportunities

  • Indian Key Celebration: Held on April 30, 2022, at 82990 Overseas Highway, focusing on indigenous plants and history.
  • Aquanauts to Astronauts: Events related to NASA and space travel.
  • Florida Keys Youth Summer Sailing & Windsurfing Camp: Outdoor educational programs for kids and teenagers.

Other Notable Florida Keys Festivals

From wild costume parties to underwater music, these festivals offer unique experiences that capture the vibrant spirit of the Keys.

Unique Experiences

  • Fantasy Fest: A 10-day extravaganza in October, including live music, pool parties, and free events.** see more info at bottom of article
  • Summer Art Show: Showcases local and international artists during the summer.
  • Underwater Music Festival: An annual event in July at Looe Key Reef.
  • Key Lime Pie Hop: Sample delicious pies from local bakeries.
  • Pub Crawl: Explore unique bars and pubs in Key West.
  • Florida Keys Birding & Wildlife Festival: Explore the region’s biodiversity through guided tours and presentations, held in various locations.

Best Time to Visit for Festivals in the Florida Keys

The Florida Keys are a year-round destination, with festivals and events taking place in every season.

However, the best time to visit largely depends on your interests and the type of festival experience you’re seeking.

Winter (December – February)

Winter is a popular time to visit the Florida Keys due to the pleasant weather, with average temperatures ranging from 60°F to 75°F.

This season hosts the Key West Fishing Tournament, which begins in December and continues until July.

The Florida Keys Seafood Festival, held annually in January, is another highlight, offering a feast of fresh seafood caught by local fishermen.

Spring (March – May)

Spring in the Florida Keys is marked by mild temperatures and lower humidity, making it an ideal time for outdoor festivals.

The Original Marathon Seafood Festival in March is a must-visit for seafood lovers.

In mid-April, the Art Festival Weekend in Key Largo celebrates local arts and culture. May brings the Key West Song Writers Festival, a treat for music lovers.

Summer (June – August)

Summer is the season for underwater music and pride celebrations. In early June, the Key West Pride festival fills the streets of Duval and Front with energy and color.

July offers a unique experience with the Underwater Music Festival at Looe Key Reef. August marks the opening of the lobster season, celebrated with the Key West Lobsterfest.

Fall (September – November)

Fall in the Florida Keys is synonymous with beer and fantasy. September hosts the Key West BrewFest, a fantastic event for craft beer enthusiasts.

In October, the Fantasy Fest transforms Key West into a hub of wild costumes, creative floats, and lively street parties.

Quick Reference Chart of Florida Keys Festivals

This comprehensive table provides an at-a-glance view of some of the most exciting festivals in the region, sorted by month.

Whether you’re interested in arts, seafood, music, or cultural celebrations, you’ll find something to suit your taste.

Check out the table below to discover the festivals, their dates, and locations, and make sure to mark your calendar for an unforgettable Florida Keys experience!

FestivalDateLocation
Florida Keys Seafood FestivalJanuaryVarious Locations
Art Under the OaksJanuaryTavernier
Original Marathon Seafood FestivalMarchMarathon
Art Festival Weekend in Key LargoMid-AprilIsland Market Place, Key Largo
Key West Song Writers FestivalMayVarious Venues, Key West
Key West PrideEarly JuneDuval and Front Streets, Key West
Underwater Music FestivalJulyLooe Key Reef
Key West LobsterfestAugustDuval Street, Key West
Key West BrewFestSeptemberSouthernmost Beach Resort
Fantasy FestOctoberVarious Locations, Key West
Hemingway DaysAnnualSloppy Joe’s Bar, Key West
WomenfestAnnualKey West
Indian Key CelebrationApril 30, 202282990 Overseas Highway
Key West Lobsterfest Street FairAug 10-13, 2023Duval Street, Key West
Key West Fishing TournamentDec – JulyKey West

Most Popular Festivals in the Florida Keys: A Closer Look

So we’ve given you a pretty long list of Florida Keys festivals, but you might be wondering – which are the most popular? Here’s an in-depth look at some of the most popular festivals that visitors flock to:

1. Fantasy Fest (October, Key West)

Fantasy Fest is a 10-day extravaganza held every October in Key West. Known for its wild costumes, creative floats, and lively street parties, this festival transforms Key West into a hub of imagination and celebration.

Highlights include the Masquerade March, the Street Fair, and the grand parade. It’s a feast for the senses and a true embodiment of Key West’s free-spirited vibe.

Please be advised that Fantasy Fest in Key West is known for its risqué and adult-themed celebrations. While the festival is a colorful and creative event that many enjoy, some of the costumes, floats, and activities may include explicit content that may not be suitable for all audiences.

If you are planning to attend Fantasy Fest, it’s important to consider the nature of the event and determine if it aligns with your comfort level and preferences. Families with children or individuals who prefer more conservative entertainment may wish to explore other festivals and events in the Florida Keys that offer a wide range of experiences to suit different tastes and sensibilities.

2. Key West Lobsterfest (August, Duval Street, Key West)

Celebrating the opening of the lobster season, Key West Lobsterfest is a seafood lover’s dream. Held on Duval Street, this festival features a lobster boil, street fair, free concert, and more.

Indulge in mouth-watering lobster dishes, enjoy live music, and immerse yourself in the festive atmosphere. It’s a culinary experience not to be missed.

3. Hemingway Days (Annual, Sloppy Joe’s Bar, Key West)

Paying homage to the legendary author Ernest Hemingway, Hemingway Days is an exciting event that features activities centered around his literary contributions and love for adventure.

Highlights include the Hemingway Look-Alike Contest, the Running of the Bulls, and the Key West Marlin Tournament. It’s a spirited celebration that captures the essence of Hemingway’s world.

4. Key West Song Writers Festival (May, Various Venues, Key West)

Shining the spotlight on over 200 talented songwriters, this festival showcases their craft across various venues in Key West.

With a free concert on Duval Street and performances in intimate settings, it’s a music lover’s paradise. Discover new talents, enjoy live performances, and celebrate the art of songwriting.

5. Key West BrewFest (September, Southernmost Beach Resort)

Craft beer enthusiasts will find their haven at the Key West BrewFest. Held at the Southernmost Beach Resort, this event offers a chance to sip brews from local and international breweries, attend beer pairing dinners, and enjoy pool parties.

Eaton Street buzzes with excitement during BrewFest, making it a must-visit for beer lovers.

6. Florida Keys Seafood Festival (January, Various Locations)

Showcasing the freshest seafood caught, cleaned, prepared, and served by local fishermen, this festival is a tribute to the region’s maritime heritage.

Enjoy a variety of seafood favorites, live music, and raffle prizes. It’s a family-friendly gathering that offers a taste of the authentic Florida Keys experience.

These festivals represent the diverse and vibrant character of the Florida Keys, each offering a unique experience that resonates with different interests and passions.

Whether it’s the artistic allure of Fantasy Fest, the culinary delights of Lobsterfest, or the literary charm of Hemingway Days, these festivals are the heart and soul of the Keys, promising unforgettable memories and encounters.

Make sure to mark your calendars and plan your visit to soak up the fun, flavors, and creativity of these iconic events.

Conclusion: Florida Keys Festivals

The Florida Keys are more than just a tropical paradise; they are a celebration of life, culture, art, nature, and community.

From the lively streets of Duval to the serene landscapes of Lower Keys, the region offers a kaleidoscope of experiences that cater to every traveler.

The festivals are a true reflection of the Keys’ vibrant spirit, each one a window into the diverse and rich tapestry that makes up this tropical haven.

From the wild and imaginative Fantasy Fest to the soulful melodies of the Key West Song Writers Festival, these events are not just celebrations; they are invitations to be part of a community that embraces diversity, creativity, and joy.

Frequently Asked Questions

What are popular festivals in the Florida Keys?

There are several popular festivals in the Florida Keys, such as the Key West Mermaid Festival in July and the Florida Keys Celtic Festival in January. These events celebrate the unique culture and atmosphere of the Florida Keys and offer a variety of exciting activities and performances for you to enjoy.

What are the dates for Fantasy Fest in Key West?

Unfortunately, I can’t provide the dates for Fantasy Fest in Key West as the information wasn’t found in the provided search results. But, Fantasy Fest is an annual event, and you can check their official website for the most updated information on dates and schedules.

Which events take place in Key Largo in 2023?

It’s difficult to provide a comprehensive list of events happening in Key Largo in 2023 based on the search results. However, you can keep an eye on local event calendars for updates on specific events as the year approaches.

What is the big festival in Key West?

One of the big festivals in Key West is Fantasy Fest. This annual event typically lasts for ten days and includes a wide range of activities, from costume contests and street fairs to extravagant parades and eccentric parties. The festival attracts thousands of visitors and locals alike, making it a must-attend event in Key West.

Any upcoming Florida Keys events this weekend?

As my search results are based on a specific date, I can’t provide information on any events happening this upcoming weekend. The best way to find upcoming events in the Florida Keys for a specific time frame is to consult local event calendars or the official websites of popular events.

What is the Fantasy Fest 2023 theme?

The Fantasy Fest theme for 2023 isn’t available in the search results. Nevertheless, each year, a new theme is announced, so make sure to check the Fantasy Fest official website for updates on the theme as the event approaches.

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